Darko Madjarovski defeated Goran Tosic 6-2 6-2 in the Serbia & Montenegro F6 round of 16 on clay. Darko Madjarovski extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-15 | Serbia F3 | R16 | clay | Goran Tosic | 7-6(6) 6-2 |
| 2007-08-20 | Serbia F5 | F | clay | Goran Tosic | 6-1 6-3 |
| 2006-07-31 | Serbia & Montenegro F3 | F | clay | Darko Madjarovski | 1-6 6-3 6-4 |
| 2006-06-26 | Serbia & Montenegro F2 | R16 | clay | Darko Madjarovski | 6-4 6-2 |